Cocaine remains a challenging synthetic target since few enantioselective methods for its construction exist. This proposal seeks to extend the scope of the 2-azaallyl anion cycloaddition methodology to the asymmetric synthesis of cocaine through the development of a novel cyclic 2-azaallyl anion. A significant advantage of the proposed route is that it is readily adaptable for the generation of novel cocaine analogs, including 6- and 7-substituted analogs and analogs with bridgehead substituents. The pharmacological profile of these analogs will be assessed by the Cocaine Treatment and Discovery Program, with the aim toward identifying analogs with cocaine antagonist activity. Such analogs may have potential use as medications for the treatment of cocaine abuse.